a single night of sex (with a man)

My first turned me  …fabulous

I’m lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from him having fucked me with my stockinged legs wrapped around his shoulders. I’m lying here, looking at the trail of clothing that marks our evening: my strap-y heels, an exquisitely hand-painted silk scarf and tube mini-skirt just inside his front door, my bangles, earrings and necklace at the far end of the bed and next to me a little camisole top and a gorgeous leather bag with its usual date-night collection of lotions, condoms, spare undies and makeup.

I know I’ll have to get up, skip into my panties and top and go to his bathroom where I’ll put myself together, but before then I will continue to lie here, grateful for the sensation of fullness that lingers for hours after a man has pulled out of me and about the memories of this evening, of our passionate kisses, his sucking on my earlobes and nipples, of my exploring his cock with my lips and my tongue, about how i love the smell of the man on my face and neck, and about his taste.

And lastly, I will think about the fact that it’s only Tuesday evening, and that there’s a whole week’s worth of men I’ve yet to meet who will want me as their sissy cum slut!

I wasn’t always like this. In fact, it was only a few years ago that the world knew me as a somewhat unremarkable guy, a hard-working, mid-30s, professional who kept pretty much to himself but who, everyone agreed, was a good guy to have as a friend. Kind, considerate, responsible. Of course, what no-one back then knew was I’d long had had a nagging question in the back of my mind on what it would be like to be in bed with another man.

I considered it a fairly simple wish; a single night of sex with another man just to say I’d “tried it.”

Like most guys of my generation and background, I’d had my share of exposure to gay sensuality. There was an old roommate who once insisted on taking me gay bar-hopping, getting me kinda drunk along the way, and launching into some pretty sloppy and wet making-out in the front seat of his car. There was the guy I met on a hiking trip who found his way into my tent one evening to give me a hand job. And a drinking buddy who an annoying habit of giving long on-the-edge-of-passionate goodnight ‘hugs’ and who finally kissed my ear and asked if I wanted more. I had always declined to reciprocate because, I told myself, it wasn’t who I was. I had girlfriends, some platonic some not, and while I could never have been considered movie-star material, I was content in my modest sex life.

Years passed, my career seemed to progress nicely enough – I still had girlfriends but to the ongoing amusement of friends and colleagues, I had yet to meet “the one. And always, in the back of my mind, sat the “what would it be like” question. Society’s openness to accepting being gay had advanced dramatically over the last decade and it became clear to me that it was finally time I did my touristic excursion into an evening of gay sex. One of the alternative newspapers in San Francisco gave me a wealth of options as I cruised through the M4M personal ads. I came across one from a “caring and supportive gentleman” – Brian was his name – “who loves to take men on their maiden voyage.”

We met at his house in a kinda posh area in Marin County, had some awkward small talk in his living room and at a point when he must have thought I was ready, led me by the hand to his backyard studio that had little more than a futon, a bed-side table with a hand-pump jar of lubricant and a tasteful little bowl of different packaged condoms.

The moment we started kissing I knew something was just very ‘right’ about this, this moment, this decision. Without thinking, I found myself un-self-consciously stripping off my T-Shirt, my jeans, and my boxers – and in doing so developed – to my surprise and undoubtedly his pleasure – a lovely hard-on. We stood there, him fully clothed and me naked, embracing, kissing, fondling. When he took me into his bed where I undressed him and found myself almost immediately sliding down to between his thighs where I began kissing. The kissing moved up. And up. And soon I was licking his shaved balls, completely comfortable with something I had never done. And then, I started on his cock. I loved every aspect of it, its smoothness, the softness of the skin and the hardness of the shaft, the cute head and the oh-so-sensitive spot just at the base of it, it’s musky sweetness. I loved how he responded and I was utterly thrilled that I was the source of that erotic pleasure.

I remember reaching around and massaging Brian’s ass, and looking up into his eyes. He smiled down at me and uttered something that will stay with me forever; “Oh you ARE a natural cocksucker aren’t you? You will soon LOVE thinking of yourself as submissive sissy… trust me!” And I found myself, in a soft almost feminine voice that came from .. who knows where? .. saying “ohhhh darling, yesss…yesss…yesss!”

We spent the next hour or so as I learned the mechanics of gay sex, but more importantly, learning something about my very essence. I went home that evening and fought back waves of emotions. What had I done? What just happened to me? What was I feeling? Was it real? Was this the real me? And maybe most tellingly, how could I put this behind me and return to my normal life? My goal, my simple wish, had been fulfilled. It was time to move on.

Two days later I got a call from Brian and he coyly asked if I would like to come by to get either trimmed or shaved ‘down there’ because “you know, it is SUCH a sexy thing for a sissy cocksucker to be totally smooth” There is was again, a reminder of how he saw me, a sissy cocksucker. The memories of those hours in his studio along with the sound of his marvelous voice made me melt and I said I could be there early that evening. I rationalized the visit that evening with him as a final gay encounter, that I would thank him for his kindness, his patience, and his gentleness.

He met me at the door wearing knit boxers that covered everything – but hid nothing, holding a glass of wine to invite me in. We embraced, kissed, he played with my nipples and rubbed me through the front of my jeans. We drank more, embraced more, and as I got increasingly horny he said “well, time for what you came for.”

Back to the studio and he took out an electric razor and started on .. my legs!

“Wait.” I cried, “I thought we were talking, you know, crotch!” He laughed and reminded me that such “gifted cocksuckers are smooth everywhere, except…” and again words that will stay with me forever – “except maybe in a little tuft of pussy fur that you’ll use to turn men.” His words flowed through me like nothing I’d never known. I was his. For Brian, my darling sexy Brian with his full lips, his firm body, his beautiful cock, I’d do anything and he could do anything to me. A half hour later I looked into a full-length mirror to see a reflection of myself with hair in precisely two spots: atop my head and within an impossibly tiny triangle surrounding my cock. It was, I was … lovely.

Over the next several months I would go back to his place at least twice weekly. For sex with him, for 3-ways, and for enjoying porn together on his huge screen TV as we masturbated each other, He was a loving and patient teacher and I began to realize how much of a willing and receptive submissive I was turning into.

We started branching out. He and I started going to gay saunas and baths, we went to sex clubs, i would don corsets and bustiers to go to fetish and fantasy dungeons, we went to costume parties, and private gatherings.

And my changes were dramatic. I was turning into an utterly fabulous queer. I started growing out my hair and going to salons for coloring and styling; i shaped my eyebrows and got full body waxes, I became skilled at makeup and my wardrobe evolved to something in between Forever 21 and Victoria’s Secret. I had become an unmistakable femmy slut. Brian loved it. I loved it. As did many – many – men.

The point of all of this is all began with a simple wish. I wanted to see what a gay encounter felt like. It was to be a one-time visit to another way of being. In fact, as I later realised, my encounter with Brian was like having a switch flipped. A switch I’d never known about but nevertheless, a switch once toggled that could never go back to where it started from.

I have become a new person. A better person. I take pride in my feminine attributes and mannerisms, I love being pretty, I love feeling the kind of power I have over men with my sensuality and I love – no – I live for – the pleasures a man can give me. I’ve begun full body electrolysis and just in case anyone doesn’t see me as the sissy I am, I’ve had large areola tattooed over my nipples and on my upper right thigh, the tattoo of a fabulous wedding garter. My unremarkable male persona is gone forever; I wake up thinking of cock, I stare at men’s bodies throughout the day and am shamelessly flirt-y whenever I can, and in the evenings i dress up in anticipation of the unbelievably satisfying eroticism of having a man who will fill my boi pussy.

My advice to all you bi- or gay-curious darlings Out There who might be thinking of the briefest of visits to ‘the other side?’ Be careful what you wish for. I’m not saying it won’t be for the best, but, be prepared for the possibility of a one-way trip to become someone very, very different.

Thank you J from Mistress Alexa – some of my favorite clients will love this!

Author: alexa

Mistress Alexa has a loinwrenching voice that hypnotizes, transfixes and controls her subjects. How long will it take her to make you feel loved? Call now: 866-57-SISSY and find out. $99 for 30 minutes.